At the tail end of a light-hearted interview with Anthony Mason for “CBS Saturday Morning,” the concert promoter Peter Shapiro said he “might be holding” Chicago’s Soldier Field for GD 60 in 2025. 

“Just in case,” Shapiro added, as the video interview concluded, spurring awkward speculative banter among Mason and the anchors of the program.

When I heard this, my first thought manifested as a bewildered utterance: Gee Dee Sixty

The moniker felt foreign spoken out loud. It also felt like something too good to be true, a pipe dream that Shapiro might have plans for but that ultimately would never come to fruition. 

But, amid a sea of things to worry about in 2022, a little speculation is like an oasis where Deadheads can ponder the epic-ness of a second Grateful Dead Fare Thee Well Tour. 

So, if GD 60 does becomes official, I think the band would have to bring back Trey Anastasio to play lead guitar. As much as I appreciate John Mayer, there is something about his pop-stardom background that doesn’t match up when assuming the role of the late, great Jerry Garcia. Maybe that’s more of a me issue; I don’t know. Every time I think of Mayer, I visualize Katy Perry singing “Firework,” and as legendary as that song may be, it does not line up with my understanding of the Grateful Dead.

I can also most definitely get behind Billy Strings playing lead guitar in GD 60. His style is riveting, steeped in bluegrass and folk. He’s a breath of youthful vigor, a student with reverence for the masters in music that came before him, and he represents the future of the jam band community. 

Strings or Anastasio would be my top picks for lead primarily because of their unique ways of emoting through the guitar, and secondly because of their background with overcoming hard drugs. I think that path, one that ultimately took the life of Jerry Garcia, is something that needs to be personally understood on a deep level when assuming the lead guitar role in the Grateful Dead. Not necessarily the off-shoot variants of the band, but if the marquee reads the Grateful Dead, then yes, the lead guitarist should have personal experience with drug abuse. That difficult road, though not admirable in any way, humbles a person so deeply that their guitar playing feels more, well, grateful — as if they are just so damn happy to be alive that they play each lick as if it is the most important of their lives, and as if it could very well be their last. 

Both Anastasio and Strings represent a new generation moved by the Dead’s music, a generation that will ostensibly carry that music into the future well after the surviving members of the Dead are gone.

But I have to admit that there is something about coming back for another “Fare Thee Well” tour that makes me uncomfortable. In 2015, Shapiro billed “Fare Thee Well: Celebrating 50 Years of the Grateful Dead” as the last time the four core surviving members of the Grateful Dead — Phil Lesh, Bob Weir, Bill Kreutzmann and Mickey Hart — would play together. And something about knowing that fact made those shows extra special. 

Nothing is meant to last forever, and that is tough to grapple with, but ultimately it is true. A painful truth that echoes in the Dead’s music, in its very name. 

So why speculate? And for what? The fact that Lesh, who survived cancer, and the other surviving members of the Grateful Dead are even touring now is a miracle, a blessing. The four of them actively travel the country through reincarnated versions of the GD experience, each bringing their own unique vibe to the art of keeping their music alive. And I am sure I can speak for all Deadheads when saying that we are immensely grateful for their continued work. Our lives are uplifted by their music in so many ways. In times of both difficulty and elation, I turn to the Grateful Dead for guidance and mystery. 

Nevertheless, one thing the pandemic taught me is that we should all spend a little more time in the present instead of planning the future. Life is so precious, and as cliche as it might sound, we all don’t know whether we’ll be here tomorrow, let alone get through the day. So why think about years ahead? 

Maybe because we all need something to look forward to, to keep us going. Saying goodbye to the Grateful Dead is hard. If this were an airport, and Lesh (82), Weir (74), Kreutzmann (76) and Hart (78) were departing on a plane, I would very much hope that they ran back and gave me one last hug before departing into the “transitive nightfall of diamonds.”

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